Indenopyridine-based compound and organic light-emitting device including the same

ABSTRACT

Provided are an indenopyridine-based compound and an organic light-emitting device including the same. The indenopyridine-based compound is represented by Formula 1:

CROSS-REFERENCE TO RELATED APPLICATIONS

This is a continuation application based on pending application Ser. No.14/457,533, filed Aug. 12, 2014, the entire contents of which is herebyincorporated by reference.

Korean Patent Application No. 10-2013-0104502, filed on Aug. 30, 2013,in the Korean Intellectual Property Office, and entitled:“Indenopyridine-Based Compound and Organic Light-Emitting DeviceIncluding The Same,” is incorporated by reference herein in itsentirety.

BACKGROUND 1. Field

One or more embodiments relate to an indenopyridine-based compound andan organic light-emitting device including the same.

2. Description of the Related Art

Organic light-emitting devices (OLEDs) are self-emitting devices thatmay have wide viewing angle, excellent contrast, quick response, highbrightness, and excellent driving voltage, and can provide multicoloredimages.

SUMMARY

Embodiments are directed to an indenopyridine-based compound representedby Formula 1:

wherein, in Formula 1,

X₁ is a nitrogen atom (N) or C(R₁₁); X₂ is N or C(R₁₂); X₃ is N orC(R₁₃); X₄ is N or C(R₁₄); wherein at least one of X₁ to X₄ is N;

L₁ is selected from a substituted or unsubstituted C₃-C₁₀ cycloalkylenegroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenylene group, asubstituted or unsubstituted C₆-C₆₀ arylene group, a substituted orunsubstituted C₂-C₁₀ heterocycloalkylene group, a substituted orunsubstituted C₂-C₁₀ heterocycloalkenylene group, and a substituted orunsubstituted C₂-C₆₀ heteroarylene group;

n1 is selected from an integer of 0, 1, 2, and 3;

R₁ and R₂ are each independently selected from a hydrogen atom, adeuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, a carboxyl group, a substituted or unsubstitutedC₁-C₃₀ alkyl group, a substituted or unsubstituted C₂-C₃₀ alkenyl group,a substituted or unsubstituted C₂-C₃₀ alkynyl group, a substituted orunsubstituted C₁-C₃₀ alkoxy group, a substituted or unsubstituted C₃-C₃₀cycloalkyl group, a substituted or unsubstituted C₃-C₃₀ cycloalkenylgroup, a substituted or unsubstituted C₆-C₃₀ aryl group, a substitutedor unsubstituted C₆-C₃₀ aryloxy group, a substituted or unsubstitutedC₆-C₃₀ arylthio group, and a substituted or unsubstituted C₂-C₃₀heteroaryl group, wherein R₁ and R₂ are optionally connected to eachother to form a substituted or unsubstituted C₆-C₂₀ saturated ring or asubstituted or unsubstituted C₆-C₂₀ unsaturated ring;

R₁₁ to R₁₄, R₃, and R₄ are each independently selected from a hydrogenatom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group,a nitro group, an amino group, a carboxyl group, a substituted orunsubstituted C₁-C₃₀ alkyl group, a substituted or unsubstituted C₂-C₃₀alkenyl group, a substituted or unsubstituted C₂-C₃₀ alkynyl group, asubstituted or unsubstituted C₁-C₃₀ alkoxy group, a substituted orunsubstituted C₃-C₃₀ cycloalkyl group, a substituted or unsubstitutedC₃-C₃₀ cycloalkenyl group, a substituted or unsubstituted C₆-C₃₀ arylgroup, a substituted or unsubstituted C₆-C₃₀ aryloxy group, asubstituted or unsubstituted C₆-C₃₀ arylthio group, and a substituted orunsubstituted C₂-C₃₀ heteroaryl group; and

a1 and a2 are each independently selected from an integer of 0, 1, 2 and3.

Also provided is an organic light-emitting device (OLED), including afirst electrode; a second electrode facing the first electrode; and anorganic layer that is disposed between the first electrode and thesecond electrode and includes an emission layer. The organic layerincludes at least one indenopyridine-based compound represented byFormula 1.

BRIEF DESCRIPTION OF THE DRAWINGS

Features will become apparent to those of skill in the art by describingin detail exemplary embodiments with reference to the attached drawingsin which:

FIG. 1 illustrates a schematic diagram illustrating an organiclight-emitting device (OLED) according to an embodiment.

DETAILED DESCRIPTION

Example embodiments will now be described more fully hereinafter withreference to the accompanying drawings; however, they may be embodied indifferent forms and should not be construed as limited to theembodiments set forth herein. Rather, these embodiments are provided sothat this disclosure will be thorough and complete, and will fullyconvey exemplary implementations to those skilled in the art.

In the drawing figures, the dimensions of layers and regions may beexaggerated for clarity of illustration. As used herein, the term“and/or” includes any and all combinations of one or more of theassociated listed items. Expressions such as “at least one of,” whenpreceding a list of elements, modify the entire list of elements and donot modify the individual elements of the list.

Provided is an indenopyridine-based compound represented by Formula 1:

In Formula 1, X₁ is N or C(R₁₁); X₂ is N or C(R₁₂); X₃ is N or C(R₁₃);X₄ is N or C(R₁₄); wherein at least one of X₁ to X₄ may be N.

In one embodiment, in Formula 1, X₁ may be N; X₂ may be C(R₁₂); X₃ maybe C(R₁₃); and X₄ may be C(R₁₄).

In another embodiment, in Formula 1, X₁ may be C(R₁₁); X₂ may be N; X₃may be C(R₁₃); and X₄ may be C(R₁₄).

In another embodiment, in Formula 1, X₁ may be C(R₁₁); X₂ may be C(R₁₂);X₃ may be N; and X₄ may be C(R₁₄).

In another embodiment, in Formula 1, X₁ may be C(R₁₁); X₂ may be C(R₁₂);X₃ may be C(R₁₃); and X₄ may be N.

In Formula 1, L₁ may be selected from a substituted or unsubstitutedC₃-C₁₀ cycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₆-C₆₀ arylenegroup, a substituted or unsubstituted C₂-C₁₀ heterocycloalkylene group,a substituted or unsubstituted C₂-C₁₀ heterocycloalkenylene group, and asubstituted or unsubstituted C₂-C₆₀ heteroarylene group.

In one embodiment, in Formula 1, L₁ may be selected from:

i) a C₃-C₁₀ cycloalkylene group, a C₃-C₁₀ cycloalkenylene group, aC₆-C₆₀ arylene group, a C₂-C₁₀ heterocycloalkylene group, a C₂-C₁₀heterocycloalkenylene group, and a C₂-C₆₀ heteroarylene group; and

ii) a C₃-C₁₀ cycloalkylene group, a C₃-C₁₀ cycloalkenylene group, aC₆-C₆₀ arylene group, a C₂-C₁₀ heterocycloalkylene group, a C₂-C₁₀heterocycloalkenylene group, and a C₂-C₆₀ heteroarylene group, eachsubstituted with at least one selected from

a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxyl group or a salt thereof, a sulfonic acidgroup or a salt thereof, a phosphoric acid group or a salt thereof, anda C₁-C₁₀ alkyl group;

a C₁-C₁₀ alkyl group substituted with at least one selected from adeuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxyl group or a salt thereof, a sulfonic acid group or asalt thereof, and a phosphoric acid group or a salt thereof;

a C₆-C₁₆ aryl group and a C₂-C₁₆ heteroaryl group; and

a C₆-C₁₆ aryl group and a C₂-C₁₆ heteroaryl group, each substituted withat least one selected from a deuterium atom, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxyl group or a salt thereof,a sulfonic acid group or a salt thereof, a phosphoric acid group or asalt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₆-C₁₆ aryl group, and a C₂-C₁₆heteroaryl group.

In another embodiment, in Formula 1, L1 may be selected from:

i) a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphtylene group, a fluorenylene group, aspiro-fluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pyrrolylene group, animidazolylene group, a pyrazolylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, anisoindolylene group, an indolylene group, an indazolylene group, apurinylene group, a quinolinylene group, a benzoquinolinylene group, aphthalazinylene group, a naphthyridinylene group, a quinoxalinylenegroup, a quinazolinylene group, a cinnolinylene group, a carbazolylenegroup, a phenanthridinylene group, an acridinylene group, aphenanthrolinylene group, a phenazinylene group, a benzooxazolylenegroup, a benzoimidazolylene group, a furanylene group, a benzofuranylenegroup, a thiophenylene group, a benzothiophenylene group, a thiazolylenegroup, an isothiazolylene group, a bezothiazolylene group, anisooxazolylene group, an oxazolylene group, a triazolylene group, atetrazolylene group, an oxzdiazolylene group, a triazinylene group, abenzooxazolylene group, a dibenzofuranylene group, adibenzothiophenylene group, and a benzocarbazolyl group; and

ii) a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphtylene group, a fluorenylene group, aspiro-fluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pyrrolylene group, animidazolylene group, a pyrazolylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, anisoindolylene group, an indolylene group, an indazolylene group, apurinylene group, a quinolinylene group, a benzoquinolinylene group, aphthalazinylene group, a naphthyridinylene group, a quinoxalinylenegroup, a quinazolinylene group, a cinnolinylene group, a carbazolylenegroup, a phenanthridinylene group, an acridinylene group, aphenanthrolinylene group, a phenazinylene group, a benzooxazolylenegroup, a benzoimidazolylene group, a furanylene group, a benzofuranylenegroup, a thiophenylene group, a benzothiophenylene group, a thiazolylenegroup, an isothiazolylene group, a bezothiazolylene group, anisooxazolylene group, an oxazolylene group, a triazolylene group, atetrazolylene group, an oxzdiazolylene group, a triazinylene group, abenzooxazolylene group, a dibenzofuranylene group, adibenzothiophenylene group, and a benzocarbazolyl group, eachsubstituted with at least one selected from

a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxyl group or a salt thereof, a sulfonic acidgroup or a salt thereof, a phosphoric acid group or a salt thereof, anda C₁-C₁₀ alkyl group;

a C₁-C₁₀ alkyl group substituted with at least one selected from adeuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxyl group or a salt thereof, a sulfonic acid group or asalt thereof, and a phosphoric acid group or a salt thereof;

a C₆-C₁₆ aryl group and a C₂-C₁₆ heteroaryl group; and

a C₆-C₁₆ aryl group and a C₂-C₁₆ heteroaryl group, each substituted withat least one selected from a deuterium atom, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxyl group or a salt thereof,a sulfonic acid group or a salt thereof, a phosphoric acid group or asalt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₆-C₁₆ aryl group, and a C₂-C₁₆heteroaryl group.

In another embodiment, in Formula 1, L1 may be selected from:

i) a phenylene group, a naphthylene group, an anthracenylene group, achrysenylene group, and a pyrenylene group; and

ii) a phenylene group, a naphthylene group, an anthracenylene group, achrysenylene group, and a pyrenylene group, each substituted with atleast one selected from

a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxyl group or a salt thereof, a sulfonic acidgroup or a salt thereof, a phosphoric acid group or a salt thereof, anda C₁-C₁₀ alkyl group;

a C₁-C₁₀ alkyl group substituted with at least one selected from adeuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxyl group or a salt thereof, a sulfonic acid group or asalt thereof, and a phosphoric acid group or a salt thereof;

a C₆-C₁₆ aryl group and a C₂-C₁₆ heteroaryl group; and

a C₆-C₁₆ aryl group and a C₂-C₁₆ heteroaryl group, each substituted withat least one selected from a deuterium atom, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxyl group or a salt thereof,a sulfonic acid group or a salt thereof, a phosphoric acid group or asalt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₆-C₁₆ aryl group, and a C₂-C₁₆heteroaryl group.

In another embodiment, in Formula 1, L1 may be selected from:

i) a phenylene group, an anthracenylene group, a chrysenylene group, anda pyrenylene group; and

ii) a phenylene group, an anthracenylene group, a chrysenylene group,and a pyrenylene group, each substituted with at least one selected from

a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, anitro group, a methyl group, an ethyl group, an n-propyl group, aniso-propyl group, an n-butyl group, a sec-butyl group, an iso-butylgroup, and a tert-butyl group;

a phenyl group, a naphthyl group, a pyridyl group, and a triazinylgroup; and

a phenyl group, a naphthyl group, a pyridyl group, and a triazinylgroup, each substituted with at least one selected from a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, amethyl group, an ethyl group, an n-propyl group, an iso-propyl group, ann-butyl group, a sec-butyl group, an iso-butyl group, and a tert-butylgroup.

In another embodiment, in Formula 1, L1 may be selected from a phenylenegroup, an anthracenylene group, a chrysenylene group, and a pyrenylenegroup.

In Formula 1, n1 denotes the number of L1, and n1 is an integer of 0 to3. When n1 is an integer of 2 or greater, L1s may be identical to ordifferent from each other.

In some embodiments, in Formula 1, n1 may be an integer of 1 or 2.

In one embodiments, in Formula 1, a moiety represented by (L₁)_(n1) maybe one selected from Formulae 2-1 to 2-4:

In Formulae 2-1 to 2-4,

Y₁ to Y₇ are each independently selected from

i) a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group,a cyano group, a nitro group, a methyl group, an ethyl group, ann-propyl group, an iso-propyl group, an n-butyl group, a sec-butylgroup, an iso-butyl group, and a tert-butyl group;

ii) a phenyl group, a naphthyl group, a pyridyl group, and a triazinylgroup; and

iii) a phenyl group, a naphthyl group, a pyridyl group, and a triazinylgroup, each substituted with at least one selected from a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, amethyl group, an ethyl group, an n-propyl group, an iso-propyl group, ann-butyl group, a sec-butyl group, an iso-butyl group, and a tert-butylgroup;

b1 to b7 are each independently an integer of 0 to 4;

* is a binding site with R₄; and

** is a binding site with an indenopyridine ring.

In another embodiment, in Formula 1, a moiety represented by (L₁)_(n1)may be one selected from Formulae 2-1 to 2-4:

In Formulae 2-1 to 2-4,

Y₁ to Y₇ are each independently selected from

a hydrogen atom, a deuterium atom, a fluorine atom, a hydroxyl group, acyano group, a nitro group, a methyl group, an ethyl group, an n-propylgroup, an iso-propyl group, a tert-butyl group, a phenyl group, anaphthyl group, a pyridyl group, and a triazinyl group;

b1 to b7 are each independently an integer of 0 or 1;

* is a binding site with R₄; and

** is a binding site with an indenopyridine ring.

In another embodiment, in Formula 1, a moiety represented by (L₁)_(n1)may be one selected from Formulae 3-1 to 3-4:

In Formulae 3-1 to 3-4,

* is a binding site with R₄; and

** is a binding site with an indenopyridine ring.

In Formula 1, R₁ and R₂ may each independently be selected from ahydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, a carboxyl group, asubstituted or unsubstituted C₁-C₃₀ alkyl group, a substituted orunsubstituted C₂-C₃₀ alkenyl group, a substituted or unsubstitutedC₂-C₃₀ alkynyl group, a substituted or unsubstituted C₁-C₃₀ alkoxygroup, a substituted or unsubstituted C₃-C₃₀ cycloalkyl group, asubstituted or unsubstituted C₃-C₃₀ cycloalkenyl group, a substituted orunsubstituted C₆-C₃₀ aryl group, a substituted or unsubstituted C₆-C₃₀aryloxy group, a substituted or unsubstituted C₆-C₃₀ arylthio group, anda substituted or unsubstituted C₂-C₃₀ heteroaryl group, wherein R₁ andR₂ may be optionally linked to each other and form a substituted orunsubstituted C₆-C₂₀ saturated ring or a substituted or unsubstitutedC₆-C₂₀ unsaturated ring.

In one embodiment, in Formula 1, R₁ and R₂ are each independentlyselected from a hydrogen atom, a deuterium atom, a halogen atom, ahydroxyl group, a cyano group, a nitro group, a substituted orunsubstituted C₁-C₁₀ alkyl group, and a substituted or unsubstitutedC₆-C₁₆ aryl group, wherein R₁ and R₂ may be optionally linked to eachother and form a substituted or unsubstituted C₆-C₂₀ saturated ring or asubstituted or unsubstituted C₆-C₂₀ unsaturated ring.

In another embodiment, in Formula 1, R₁ and R₂ are each independentlyselected from a hydrogen atom, a deuterium atom, a fluorine atom, ahydroxyl group, a cyano group, a nitro group, a methyl group, an ethylgroup, an n-propyl group, an iso-propyl group, a tert-butyl group, aphenyl group, and a naphthyl group, wherein R₁ and R₂ may be optionallylinked to each other and form an unsubstituted C₆-C₂₀ saturated ring oran unsubstituted C₆-C₂₀ unsaturated ring.

In another embodiment, in Formula 1, R₁ and R₂ may each independently beselected from a hydrogen atom, a deuterium atom, a methyl group, and aphenyl group, or R₁ and R₂ combined are Formula 5:

In Formula 5, * is a binding site with an indenopyridine ring.

In Formula 1, R₁₁ to R₁₄, R₃, and R₄ may each independently be selectedfrom a hydrogen atom, a deuterium atom, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, an amino group, a carboxyl group, asubstituted or unsubstituted C₁-C₃₀ alkyl group, a substituted orunsubstituted C₂-C₃₀ alkenyl group, a substituted or unsubstitutedC₂-C₃₀ alkynyl group, a substituted or unsubstituted C₁-C₃₀ alkoxygroup, a substituted or unsubstituted C₃-C₃₀ cycloalkyl group, asubstituted or unsubstituted C₃-C₃₀ cycloalkenyl group, a substituted orunsubstituted C₆-C₃₀ aryl group, a substituted or unsubstituted C₆-C₃₀aryloxy group, a substituted or unsubstituted C₆-C₃₀ arylthio group, anda substituted or unsubstituted C₂-C₃₀ heteroaryl group.

In one embodiment, in Formula 1, R₁₁ to R₁₄ and R₃ may eachindependently be selected from

i) a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group,a cyano group, a nitro group, a methyl group, an ethyl group, ann-propyl group, an iso-propyl group, an n-butyl group, a sec-butylgroup, an iso-butyl group, and a tert-butyl group;

ii) a phenyl group, a naphthyl group, a pyridyl group, and a triazinylgroup; and

iii) a phenyl group, a naphthyl group, a pyridyl group, and a triazinylgroup, each substituted with at least one selected from a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, amethyl group, an ethyl group, an n-propyl group, an iso-propyl group, ann-butyl group, a sec-butyl group, an iso-butyl group, and a tert-butylgroup.

In another embodiment, in Formula 1, R₁₁ to R₁₄ and R₃ may eachindependently be selected from a hydrogen atom, a deuterium atom, afluorine atom, a cyano group, a nitro group, a methyl group, an ethylgroup, an n-propyl group, an iso-propyl group, an n-butyl group, asec-butyl group, and an iso-butyl group.

In another embodiment, in Formula 1, R₁₁ to R₁₄ and R₃ may eachindependently be selected from a hydrogen atom, a deuterium atom, afluorine atom, a cyano group, a nitro group, a methyl group, and atert-butyl group.

In one embodiment, in Formula 1, R₄ may be selected from a substitutedor unsubstituted C₆-C₂₀ aryl group, and a substituted or unsubstitutedC₂-C₂₀ heteroaryl group.

In another embodiment, in Formula 1, R₄ may be selected from:

i) a C₆-C₂₀ aryl group and a C₂-C₂₀ heteroaryl group; and

ii) a C₆-C₂₀ aryl group and a C₂-C₂₀ heteroaryl group, each substitutedwith at least one selected from

a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxyl group or a salt thereof, a sulfonic acidgroup or a salt thereof, a phosphoric acid group or a salt thereof, anda C₁-C₁₀ alkyl group;

a C₁-C₁₀ alkyl group substituted with at least one selected from adeuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxyl group or a salt thereof, a sulfonic acid group or asalt thereof, and a phosphoric acid group or a salt thereof;

a C₆-C₁₆ aryl group and a C₂-C₁₆ heteroaryl group; and

a C₆-C₁₆ aryl group and a C₂-C₁₆ heteroaryl group, each substituted withat least one selected from a deuterium atom, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxyl group or a salt thereof,a sulfonic acid group or a salt thereof, a phosphoric acid group or asalt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₆-C₁₆ aryl group, and a C₂-C₁₆heteroaryl group.

In another embodiment, in Formula 1, R₄ may be selected from:

i) a phenyl group, a pentalenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphtyl group, afluorenyl group, a spiro-fluorenyl group, a phenalenyl group, aphenathrenyl group, an anthryl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenylgroup, a picenyl group, a perylenyl group, a pentaphenyl group, ahexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolylgroup, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, apyridazinyl group, an isoindolyl group, an indolyl group, an indazolylgroup, a purinyl group, a quinolinyl group, a benzoquinolinyl group, aphthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzooxazolyl group, a benzoimidazolyl group, afuranyl group, a benzofuranyl group, a thiophenyl group, abenzothiophenyl group, a thiazolyl group, an isothiazolyl group, abenzothiazolyl group, an isoxazolyl group, an oxazolyl group, atriazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a benzooxazolyl group, a dibenzopuranyl group, adibenzothiophenyl group, and a carbazolyl group; and

ii) a phenyl group, a pentalenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphtyl group,fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, aphenathrenyl group, an anthryl group, fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenylgroup, a picenyl group, a perylenyl group, a pentaphenyl group, ahexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolylgroup, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, apyridazinyl group, an isoindolyl group, an indolyl group, an indazolylgroup, a purinyl group, a quinolinyl group, a benzoquinolinyl group, aphthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzooxazolyl group, a benzoimidazolyl group, afuranyl group, a benzofuranyl group, a thiophenyl group, abenzothiophenyl group, a thiazolyl group, an isothiazolyl group, abenzothiazolyl group, an isoxazolyl group, an oxazolyl group, atriazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a benzooxazolyl group, a dibenzopuranyl group, adibenzothiophenyl group, and a carbazolyl group, each substituted withat least one selected from

a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxyl group or a salt thereof, a sulfonic acidgroup or a salt thereof, a phosphoric acid group or a salt thereof, anda C₁-C₁₀ alkyl group;

a C₁-C₁₀ alkyl group substituted with at least one selected from adeuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxyl group or a salt thereof, a sulfonic acid group or asalt thereof, and a phosphoric acid group or a salt thereof;

a C₆-C₁₆ aryl group and a C₂-C₁₆ heteroaryl group; and

a C₆-C₁₆ aryl group and a C₂-C₁₆ heteroaryl group, each substituted withat least one selected from a deuterium atom, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxyl group or a salt thereof,a sulfonic acid group or a salt thereof, a phosphoric acid group or asalt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₆-C₁₆ aryl group, and a C₂-C₁₆heteroaryl group.

In another embodiment, in Formula 1, R₄ may be selected from:

i) a phenyl group, a naphthyl group, and an anthryl group; and

ii) a phenyl group, a naphthyl group, and an anthryl group, eachsubstituted with at least one selected from a hydrogen atom, a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, amethyl group, an ethyl group, an n-propyl group, an iso-propyl group, atert-butyl group, a phenyl group, a naphthyl group, and an anthrylgroup.

In another embodiment, in Formula 1, R₄ may be selected from a phenylgroup, 1-a naphthyl group, and 2-a naphthyl group.

In Formula 1, a1 is the number of R3 which may be an integer of 0 to 3.When a1 is an integer of 2 or greater, R3s may be identical to ordifferent from each other.

In Formula 1, a2 is the number of R4 which may be an integer of 0 to 3.When a2 is an integer of 2 or greater, R4s may be identical to ordifferent from each other.

In some embodiments, in Formula 1, a1 may be an integer of 0 or 1.

In some embodiments, in Formula 1, a2 may be an integer of 0 or 1.

In Formula 1, the number of moiety represented by [(R₄)_(a2)-(L₁)_(n1)]may be represented by (4-a1).

In one embodiment, a1 may be an integer of 2 or 3.

In another embodiment, a2 may be 1 or n1 may be 1, and a1 may be 3.

In one embodiment, the indenopyridine-based compound may be representedby Formula 1a:

wherein, in Formula 1a, a moiety represented by (L₁)_(n1) may be oneselected from Formulae 3-1 to 3-4:

wherein, in Formulae 3-1 to 3-4,

* is a binding site with R₄; ** is a binding site with an indenopyridinering; and

R₁ and R₂ are each independently selected from a hydrogen atom, adeuterium atom, a methyl group, and a phenyl group, or R₁ and R₂combined are Formula 5:

wherein, in Formula 5,

* is a binding site with an indenopyridine ring;

R₃ and R₁₂ to R₁₄ are each independently selected from a hydrogen atom,a deuterium atom, a fluorine atom, a cyano group, a nitro group, and amethyl group;

R₄ is selected from a phenyl group, a 1-naphthyl group, and a 2-naphthylgroup;

a1 is 3; and

a2 is an integer of 0 or 1.

In another embodiment, the indenopyridine-based compound may berepresented by one selected from Formulae 1b to 1e:

wherein, in Formulae 1b to 1e, a moiety represented by (L₁)_(n1) is oneselected from Formulae 3-1 to 3-4:

wherein, in Formulae 3-1 to 3-4,

* is a binding site with R₄; ** is a binding site with an indenopyridinering; and

R₁ and R₂ are each independently selected from a hydrogen atom, adeuterium atom, a methyl group, and a phenyl group, or R₁ and R₂combined are Formula 5:

wherein, in Formula 5,

* is a binding site with an indenopyridine ring;

R₁₃ is selected from a hydrogen atom, a deuterium atom, a fluorine atom,a cyano group, a nitro group, and a methyl group;

R₄ is selected from a phenyl group, a 1-naphthyl group, and a 2-naphthylgroup; and

a2 is an integer of 0 or 1.

In some embodiments, the indenopyridine-based compound may be selectedfrom Compounds 1 to 25:

An indenopyridine-based compound represented by Formula 1 may have ahigh glass transition temperature (Tg) and excellent thermal stability,and an OLED including an indenopyridine-based compound represented byFormula 1 may have a thin film that exhibits high stability.

An indenopyridine-based compound represented by Formula 1 may increase aformation ratio of excitons by increasing a trapping ratio of holes andelectrons in an OLED. Also, an indenopyridine-based compound representedby Formula 1 may have a relatively high resistance against a chargeexposure, and an OLED including an indenopyridine-based compoundrepresented by Formula 1 may have an improved efficiency and an improvedlifespan.

An indenopyridine-based compound represented by Formula 1 may have aband gap that is narrower than that of a carbazole-based compound, andmay help provide improved emission of fluorescent light compared to acarbazole-based compound. In addition, the indenopyridine-based compoundmay have excellent hole transporting properties, and theindenopyridine-based compound may help provide an OLED with an improvedefficiency compared to a carbazole-based compound, which may hindercontrol of charge balance in an emission layer.

Also, an indenopyridine-based compound represented by Formula 1 may havea higher amorphous degree than a compound including pyridine, and theindenopyridine-based compound may produce excitons with betterefficiency in an emission layer. An organic-light emitting deviceincluding the indenopyridine-based compound may have a relatively highefficiency.

Moreover, an indenopyridine-based represented by Formula 1 includes anitrogen atom (N) in an indenopyridine ring, and charges may be easilytrapped in the indenopyridine-based compound. Therefore, when theindenopyridine-based compound serves as a host, a large amount ofcharges trapped in the host may be transported to a dopant, andefficiency of the OLED may increase.

An indenopyridine-based compound represented by Formula 1 may besynthesized by using an organic synthesis method. The synthesis methodof the indenopyridine-based compound may be easily understood by one ofskill in the art with reference to examples, which will be describedbelow.

As used herein, the expression “organic layer” refers to a single layerand/or multiple layers disposed between a first electrode and a secondelectrode of an OLED.

At least one indenopyridine-based compound represented by Formula 1 maybe included in an organic layer disposed between a pair of electrodes ofan OLED. For example, the at least one indenopyridine-based compoundrepresented by Formula 1 may be included in an emission layer. The atleast one indenopyridine-based compound represented by Formula 1 mayserve as a host of the emission layer.

In an embodiment, provided is an OLED including a first electrode; asecond electrode facing the first electrode; and an organic layer thatis disposed between the first electrode and the second electrode andincludes an emission layer, wherein the organic layer includes theindenopyridine-based compound represented by Formula 1.

As used herein, the expression “(the organic layer) may include at leastone indenopyridine-based compound of Formula 1” may be understood as“(the organic layer) may include one indenopyridine-based compoundrepresented by Formula 1 or at least two different compounds selectedfrom indenopyridine-based compounds represented by Formula 1”.

In some embodiments, the organic layer may only include Compound 1 asthe indenopyridine-based compound. For example, Compound 1 may beincluded in the emission layer of the organic light-emitting device.Alternatively, the organic layer may include Compound 1 and Compound 2as the indenopyridine-based compound. For example, Compound 1 andCompound 2 may be included in the same layer or respectively included intwo different layers (e.g., an emission layer or a first emission layerand a second emission layer).

FIG. 1 illustrates a schematic cross-sectional view of an OLED 100according to an embodiment. Hereinafter, a structure and a manufacturingmethod of an OLED will be described in more detail with reference toFIG. 1.

A substrate 110 may be a substrate used in a general OLED, and may be aglass substrate or a transparent plastic substrate having excellentmechanical strength, thermal stability, transparency, surfacesmoothness, ease of handling, and waterproofness.

A first electrode 120 may be formed by applying a first electrodematerial on the substrate 110 by deposition or sputtering. In anembodiment, the first electrode 120 is an anode, and the first electrodematerial may be selected from materials having a high work function tofacilitate hole injection. The first electrode 120 may be a reflectiveelectrode or a transparent electrode. Examples of the first electrodematerial may include indium-tin oxide (ITO), Indium-zinc-oxide (IZO),tin oxide (SnO₂), and zinc oxide (ZnO). Also, in an embodiment,magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca),magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) is used as thefirst electrode material, and the first electrode 120 may be formed as areflective electrode.

The first electrode 120 may be formed as a single layer or may have amulti-layered structure having at least two layers. For example, thefirst electrode 120 may have a three-layered structure, e.g.,ITO/Ag/ITO.

An organic layer 130 is formed on the first electrode 120.

The organic layer 130 may sequentially include a hole injection layer(HIL) 131, a hole transport layer (HTL) 132, a H-functional layer, abuffer layer, an emission layer (EML) 133, an electron transport layer(ETL) 134, and an electron injection layer (EIL) 135.

The HIL 131 may be formed on the first electrode 120 by using variousmethods such as vacuum deposition, spin coating, casting, or LBdeposition.

When the HIL 131 is formed by vacuum deposition, the depositionconditions may vary according to a compound used as a material forforming the HIL 131 and a structure and thermal characteristics of adesired HIL. For example, the deposition condition may be a depositiontemperature of about 100 to about 500° C., a degree of vacuum of about10⁻⁸ to about 10⁻³ torr, and a deposition speed of about 0.01 to about100 Å/sec.

When the HIL 131 is formed by spin coating, the coating condition mayvary according to a compound used as a material for forming the HIL 131,a structure of a desired HIL, and thermal characteristics. For example,the coating condition may be a coating speed of about 2,000 to about5,000 rpm and a heat treatment temperature for removing a solvent aftercoating of about 80 to about 200° C.

Exemplary materials for forming the HIL 131 includeN,N′-diphenyl-N,N′-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4′-diamine(DNTPD), a phthalocyanine compound such as copper phthalocyanine,4,4′,4″-tris(3-methylphenylphenylamino) triphenylamine (m-MTDATA),N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPB),4,4′,4″-tris(N,N-diphenylamino) triphenylamine) (TDATA),4,4′,4″-tris[2-naphthyl(phenyl)amino] triphenylamine) (2-TNATA),polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonicacid (PANI/CSA), andpolyaniline/poly(4-styrenesulfonate) (PANI/PSS):

A thickness of the HIL 131 may be in a range of about 100 Å to about10,000 Å, for example, in a range of about 100 Å to about 1,000 Å.Maintaining a thickness of the HIL 131 within this range may helpprovide satisfactory hole injecting properties without a substantialincrease in driving voltage.

Next, the HTL 132 may be formed on the HTL 131 by vacuum deposition,spin coating, casting, or LB deposition. When the HTL is formed byvacuum deposition or spin coating, the deposition and coating conditionsvary depending on a used compound, but generally the conditions may beabout the same as the conditions for forming the HIL 131.

Exemplary materials for forming the HTL 131 include carbazolederivatives, such as N-phenylcarbazole and polyvinylcarbazole,N,N-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine (TPD),4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), andN,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPB):

A thickness of the HTL 132 may be in a range of about 50 Å to about2,000 Å, for example, in a range of about 100 Å to about 1,500Å.Maintaining a thickness of the HTL 132 within this range may helpprovide satisfactory hole transporting properties without a substantialincrease in driving voltage.

The H-functional layer (a functional layer having both hole injectionand transport abilities) may include at least one of the HIL materialsand the HTL materials stated above, and a thickness of the H-functionallayer may be in a range of about 500 Å to about 10,000 Å, for example,in a range of about 100 Å to about 1,000Å. Maintaining a thickness ofthe H-functional layer within this range may help provide satisfactoryhole injecting and transporting properties without a substantialincrease in driving voltage.

At least one of the HIL 131, the HTL 132, and the H-functional layer mayinclude at least one of a compound represented by Formula 300 and acompound represented by Formula 350:

<Formula 300>

In Formulae 300 and 350, Ar₁₁, Ar₁₂, Ar₂₁, and Ar₂₂ are eachindependently a substituted or unsubstituted C₅-C₆₀ arylene group.Detailed descriptions about Ar₁₁, Ar₁₂, Ar₂₁, and Ar₂₂ may be referredto the detailed description of L₁ stated above.

In Formula 300, e and f are each independently an integer of 0 to 5, forexample, 0, 1, or 2. In one embodiment, e may be 1, and f may be 0.

In Formulae 300 and 350, R₅₁ to R₅₈, R₆₁ to R₆₉, R₇₁, and R₇₂ may eachindependently be a hydrogen atom, a deuterium atom, a halogen atom, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxyl group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a substituted or unsubstituted C₁-C₆₀ alkylgroup, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₆₀cycloalkyl group, a substituted or unsubstituted C₅-C₆₀ aryl group, asubstituted or unsubstituted C₅-C₆₀ aryloxy group, or a substituted orunsubstituted C₅-C₆₀ arylthio group. In some embodiments, R₅₁ to R₅₈,R₆₁ to R₆₉, R₇₁, and R₇₂ may each independently be one of:

a hydrogen atom; a deuterium atom; a halogen atom; a hydroxyl group; acyano group; a nitro group; an amino group; an amidino group; ahydrazine group; a hydrazone group; a carboxyl group or a salt thereof;a sulfonic acid group or a salt thereof; a phosphoric acid group or asalt thereof; a C₁-C₁₀ alkyl group (e.g., a methyl group, an ethylgroup, a propyl group, a butyl group, a pentyl group, or a hexyl group);and a C₁-C₁₀ alkoxy group (e.g., a methoxy group, an ethoxy group, apropoxy group, a butoxy group, or a pentoxy group);

a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group, each substituted with atleast one of a deuterium atom, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, and a phosphoric acid group or a saltthereof;

a phenyl group; a naphthyl group; an anthryl group; a fluolenyl group;and a pyrenyl group; and

a phenyl group, a naphthyl group, an anthryl group, a fluolenyl group,and a pyrenyl group, each substituted with at least one of a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀ alkylgroup, and a C₁-C₁₀ alkoxy group.

In Formula 300, R₅₉ may be one of:

a phenyl group; a naphthyl group; an anthryl group; a biphenyl group;and a pyridyl group; and

a phenyl group, a naphthyl group, an anthryl group, a biphenyl group,and a pyridyl group, each substituted with at least one of a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a substituted orunsubstituted C₁-C₂₀ alkyl group, and a substituted or unsubstitutedC₁-C₂₀ alkoxy group.

In some embodiments, a compound represented by Formula 300 may berepresented by Formula 300A:

In Formula 300A, detailed descriptions about R₅₁, R₆₁, R₆₂, and R₅₉ areas stated above.

In some embodiments, at least one of the HIL 131, the HTL 132, and theH-functional layer may include at least one of Compounds 301 to 320:

The at least one of the HIL 131, the HTL 132, and the H-functional layermay further include a charge-generating material in addition to the HILmaterial, the HTL material, and/or a material having both hole injectingand transporting capabilities to increase conductivity of the layers.

The charge-generating material may be, for example, one of a quininederivative, a metal oxide, and a cyano-containing compound. Examples ofcharge-generating material include quinone derivatives, such astetra-cyanoquinodimethane (TCNQ) and2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); metaloxides, such as a tungsten oxide and a molybdenum oxide; andcyano-containing compounds, such as Compound 100 (HAT-CN):

When the HIL 131, the HTL 132, and the H-functional layer furtherinclude the charge-generating material, the charge-generating materialmay be homogeneously or unhomogeneously dispersed in the HIL 131, theHTL 132, and the H-functional layer.

The buffer layer may be disposed between the at least one of the HIL131, the HTL 132, and the H-functional layer and the EML 133. The bufferlayer increases efficiency by compensating an optical resonance distanceaccording the wavelength of light emitted from the EML 133. The bufferlayer may include an HIL material and an HTL material. Also, the bufferlayer may include the same material as one of the materials included inthe HIL 131, the HTL 132, and the H-functional layer formed under thebuffer layer.

The EML 133 may be formed on the HIL 131, the HTL 132, the H-functionallayer, or the buffer layer by vacuum deposition, spin coating, casting,or LB deposition. When the EML is formed by vacuum deposition or spincoating, the deposition and coating conditions vary according to a usedcompound, but generally the condition may be about the same as thecondition for forming the HIL 131.

The EML 133 may include an EML material. In some embodiments, the EML133 may include an indenopyridine-based compound represented byFormula 1. The indenopyridine-based compound represented by Formula 1may serve as a host.

Also, the EML 133 may further include a host and a dopant.

Examples of the host include Alq₃, 4,4′-N,N′-dicabazole-biphenyl (CBP),poly(n-vinylcabazole) (PVK), 9,10-di(naphthalene-2-yl)anthracene (DNA),TCTA, 1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBI),3-tert-butyl-9,10-di(naphth-2-yl) anthracene (TBADN), E3, anddistyrylarylene (DSA), dmCBP (refer to the formula below), and Compounds501 through 509 below:

Also, the host may be an anthracene-based compound represented byFormula 400 below:

In Formula 400, Ar₁₁₁ and Ar₁₁₂ may each independently be a substitutedor unsubstituted C₅-C₆₀ arylene group; Ar₁₁₃ through Ar₁₁₆ may eachindependently be selected from a substituted or unsubstituted C₁-C₁₀alkyl group and a substituted or unsubstituted C₅-C₆₀ aryl group; and g,h, i, and j may each independently be an integer of 0 to 4.

For example, in Formula 400, Ar₁₁₁ and Ar₁₁₂ may each independently be:

a phenylene group, a naphthylene group, a phenanthrenylene group or apyrenylene group; or

a phenylene group, a naphthylene group, a phenanthrenylene group,fluolenyl group, or a pyrenylene group, each substituted with at leastone of a phenyl group, a naphthyl group, and an anthryl group.

In Formula 400, g, h, i, and j are each independently an integer of 0,1, or 2.

In Formula 400, Ar₁₁₃ to Ar₁₁₆ may each independently be one of:

a C₁-C₁₀ alkyl group substituted with at least one of a phenyl group, anaphthyl group, and an anthryl group;

a phenyl group; a naphthyl group; an anthryl group; a pyrenyl group; aphenathrenyl group; a fluolenyl group;

a phenyl group, a naphthyl group, an anthryl group, a pyrenyl group, aphenathrenyl group, and a fluolenyl group, each substituted with atleast one of a deuterium atom, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group,a pyrenyl group, a phenathrenyl group, and a fluolenyl group; and

In some embodiments, the anthracene-based compound of Formula 400 may beone of the compounds below:

Also, an anthracene-based compound represented by Formula 401 below maybe used as the host:

In Formula 401, detailed descriptions of Ar₁₂₂ through Ar₁₂₅ may bereferred to the description of Ar₁₁₃ of Formula 400 stated above.

In Formula 401, Ar₁₂₆ and Ar₁₂₇ may each independently be a C₁-C₁₀ alkylgroup (e.g., a methyl group, an ethyl group, or a propyl group).

In Formula 401, k and l may each independently be an integer of 0 to 4.For example, k and l may each independently be 0, 1, or 2.

For example, the anthrecene-based compound of Formula 401 may be one ofthe following compounds:

For example, a blue dopant may be one of terfluorene and compoundsrepresented by the formulae below:

For example, a red dopant may be one of the compounds below:

For example, a green dopant may be one of the compounds below:

Examples of a dopant included in the EML include the organic metalcomplexes below:

Also, the dopant may be represented by Formula 100:

In Formula 100, X is selected from a substituted or unsubstituted C₉-C₁₀cycloalkylene group, a substituted or unsubstituted C₉-C₁₀cycloalkenylene group, and a substituted or unsubstituted C₉-C₆₀ arylenegroup; Ar₁₀₁ and Ar₁₀₂ are each independently selected from asubstituted or unsubstituted C₆-C₃₀ aryl group and a substituted orunsubstituted C₂-C₃₀ heteroaryl group; and n is an integer of 2 to 4.

In one embodiment, in Formula 100, X may be selected from:

i) an anthracenyl group, a chrysenyl group, a pyrenyl group, and abenzopyrenyl group; and

ii) an anthracenyl group, a chrysenyl group, a pyrenyl group, and abenzopyrenyl group, each substituted with at least one selected from adeuterium atom, a fluorine atom, a cyano group, a nitro group, a methylgroup, an ethyl group, an n-propyl group, an iso-propyl group, ann-butyl group, a sec-butyl group, an iso-butyl group, and a tert-butylgroup.

In another embodiment, in Formula 100, X may be selected from ananthracenyl group, a chrysenyl group, a pyrenyl group, and abenzopyrenyl group.

In another embodiment, in Formula 100, X may be a pyrenylene group.

In one embodiment, in Formula 100, Ar₁₀₁ and Ar₁₀₂ may eachindependently be selected from:

i) a phenyl group, a naphthyl group, and a biphenyl group; and

ii) a phenyl group, a naphthyl group, and a biphenyl group, eachsubstituted with at least one selected from a deuterium atom, a fluorineatom, a cyano group, a nitro group, a methyl group, an ethyl group, ann-propyl group, an iso-propyl group, an n-butyl group, a sec-butylgroup, an iso-butyl group, a tert-butyl group, and a phenyl group.

In another embodiment, in Formula 100, Ar₁₀₁ and Ar₁₀₂ may eachindependently be selected from:

i) a phenyl group and a biphenyl group; and

ii) a phenyl group and a biphenyl group, each substituted with at leastone selected from a fluorine atom, a methyl group, and a phenyl group.

In one embodiment, in Formula 100, n may be 2.

In some embodiments, a compound represented by Formula 100 may be oneselected from Compounds 101 to 109:

When the EML 133 includes a host and a dopant, an amount of the dopantin the EML 133 may be generally in the range of, for example, about 0.01to about 15 wt % based on 100 wt % of the host.

A thickness of the EML 133 is in a range of about 200 Å to about 700 Å.Maintaining a thickness of the EML 133 within this range may helpprovide excellent light-emitting properties without a substantialincrease in driving voltage.

When the OLED 100 is a full-color OLED, the EML 133 may be patterned asa red EML, a green EML, and a blue EML depending on a red pixel, a greenpixel, and a blue pixel. In an embodiment, the indenopyridine-basedcompound represented by Formula 1 may be included in the blue EML as ahost.

The EML 133 may have a multiple-layered structure, in which a red EML, agreen EML, and a blue EML are stacked so as to emit white light, or theEML 133 may have a single-layered structure including all of a redlight-emitting material, a green light-emitting material, and a bluelight-emitting material. The OLED 100 including the EML 133 may emitlight in full-color by further including a red color filter, a greencolor filter, and a blue color filter.

Next, the ETL 134 may be formed on the EML 133 by vacuum deposition,spin coating, or casting. When the ETL 134 is formed by vacuumdeposition or spin coating, the deposition and coating conditions varydepending on a used compound, but generally the conditions may be aboutthe same as the conditions for forming the HIL 131. Exemplary materialsfor forming the ETL include quinoline derivatives such astris(8-quinolinolate)aluminum (Alq₃),3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole(TAZ), bis(2-methyl-8-quinolinolato-N1,O8)-(1,1′-biphenyl) (Balq),beryllium bis(benzoquinolin-10-olate) (Bebq₂), DNA, Compound 301,Compound 302, and Bphen:

A thickness of the ETL 134 may be in a range of about 100 Å to about1,000 Å, for example, in a range of about 150 Å to about 500 Å.Maintaining a thickness of the ETL 134 within this range may helpprovide satisfactory electron transporting properties without asubstantial increase in driving voltage.

The ETL 134 may further include a metal-containing material in additionto an electron transporting organic compound. The metal-containingmaterial may include a Li-complex. Examples of the Li-complex mayinclude a lithium quinolate (Liq) or Compound 203:

Also, the EIL 135, which facilitates electron injection from a cathode,may be formed on the ETL 134. Exemplary materials for forming the EIL135 include LiF, NaCl, CsF, Li₂O, or BaO. The deposition condition ofthe EIL may vary according a used compound, but generally the conditionmay be about the same as the condition for forming the HIL 131.

A thickness of the EIL 135 may be in a range of about 1 Å to about 100Å, for example, in a range of about 3 Å to about 90 Å. Maintaining athickness of the EIL 135 within this range may help provide satisfactoryelectron injecting properties without a substantial increase in drivingvoltage.

The second electrode 140 is formed on the organic layer 130. The secondelectrode 140 may be a cathode, which is an electron injectionelectrode. In an embodiment, a metal for forming the second electrode140 may include a metal having low work function, such as metal, analloy, an electric conducting compound, and mixtures thereof. Forexample, the second electrode 140 may be formed as a thin film by usinglithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li),calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag), andmay be transparent. In order to obtain a top-emission type OLED, thesecond electrode 140 may be formed as a transparent electrode by usingITO or IZO.

Also, in an embodiment, a phosphorescent dopant is included in the EML133, and a hole blocking layer (HBL) may be formed between the ETL 134and the EML 133 or between the H-functional layer and the EML 133 byvacuum deposition, spin coating, casting or LB deposition to helpprevent triplet excitons or holes from being diffused to the ETL 134.When the HBL is formed by vacuum deposition or spin coating, theconditions thereof may vary according to a used compound, but generallythe conditions may be about the same as the condition for forming theHIL 131. Exemplary HBL materials include an oxadiazole deriative, atriazole derivative, and a phenanthroline derivative. For example, BCPmay be used as a HBL material:

A thickness of the HBL may be in a range of about 20 Å to about 1,000 Å,for example, in a range of about 30 Å to about 300 Å. Maintaining athickness of the HBL is within this range may help provide excellenthole blocking properties without a substantial increase in drivingvoltage.

The OLED 100 has been described by referring to FIG. 1. Additionalembodiments include omission of one or more of the layers illustrated inFIG. 1 (i.e., EIL, ETL, EML, HTL, and HIL), rearrangement of one or moreof the layers illustrated in FIG. 1, and/or additional layers.

As used herein, examples of the unsubstituted C₁-C₆₀ alkyl group (or aC₁-C₆₀ alkyl group) include linear or branched C₁-C₆₀ alkyl groups suchas methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl,and the like. Examples of the substituted C₁-C₆₀ alkyl group include agroup, in which at least one hydrogen in the unsubstituted C₁-C₆₀ alkylgroup is substituted with one of

a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxyl group or a salt thereof, a sulfonic acid ora salt thereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one of adeuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxyl group or a salt thereof, a sulfonic acid or a saltthereof, and a phosphoric acid or a salt thereof;

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, and a C₂-C₆₀heteroaryl group;

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, and a C₂-C₆₀heteroaryl group), each substituted with at least one of a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxyl group or a salt thereof, a sulfonic acid or a salt thereof, aphosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a phenylgroup, a naphthyl group, an anthryl group, a fluolenyl group, adimethylfluolenyl group, a diphenylfluolenyl group, a carbazolyl group,a phenylcarbazolyl group, a pyridyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolylgroup, and an isoquinolyl group; and

—N(Q₁₁)(Q₁₂); and —Si(Q₁₃)(Q₁₄)(Q₁₅) (here, Q₁₁ and Q₁₂ are eachindependently a C₆-C₆₀ aryl group or a C₂-C₆₀ heteroaryl group, and Q₁₃to Q₁₅ are each independently a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxygroup, a C₆-C₆₀ aryl group, or C₂-C₆₀ heteroaryl group.

As used herein, the unsubstituted C₁-C₆₀ alkoxy group (or C₁-C₆₀ alkoxygroup) has a formula of —OA (in this regard, A is the unsubstitutedC₁-C₆₀ alkyl group as described above) and examples thereof includemethoxy, ethoxy, isopropyloxy, and the like. At least one hydrogen atomof the unsubstituted C₁-C₆₀ alkoxy group may be substituted with thesame substituent as in the substituted C₁-C₆₀ alkyl group describedabove.

As used herein, the unsubstituted C₂-C₆₀ alkenyl group (or C₂-C₆₀alkenyl group) is interpreted to contain at least one carbon-carbondouble bond in the center or at a terminal of the unsubstituted C₂-C₆₀alkyl group. Examples of the unsubstituted C₂-C₆₀ alkenyl group includeethenyl, propenyl, butenyl, and the like. At least one hydrogen atom ofthe C₂-C₆₀ alkenyl group may be substituted with the same substituent asin the substituted C₁-C₆₀ alkyl group described above.

As used herein, the unsubstituted C₂-C₆₀ alkynyl group (or C₂-C₆₀alkynyl group) is interpreted to contain at least one carbon-carbontriple bond in the center or at a terminal of the C₂-C₆₀ alkyl groupdefined above. Examples of the unsubstituted C₂-C₆₀ alkynyl groupinclude ethynyl, propynyl, and the like. At least one hydrogen atom ofthe unsubstituted C₂-C₆₀ alkynyl group may be substituted with the samesubstituent as in the substituted C₁-C₆₀ alkyl group described above.

As used herein, the unsubstituted C₃-C₃₀ cycloalkyl group indicates amonovalent group of a saturated cyclic hydrocarbon having 3 to 30carbons. Examples of the unsubstituted C₃-C₃₀ cycloalkyl group include acyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexylgroup, and a cyclooctyl group. At least one hydrogen atom of theunsubstituted C₃-C₃₀ cycloalkyl group may be substituted with the samesubstituent as in the substituted C₁-C₆₀ alkyl group described above.

As used herein, the unsubstituted C₃-C₃₀ cycloalkenyl group indicates aring-type unsaturated hydrocarbon group including at least onecarbon-carbon double bond, but not an aromatic ring. Examples of theunsubstituted C₃-C₃₀ cycloalkenyl group include a cyclopropenyl group, acyclobutenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a 1,3-cyclohexadienyl group, a 1,4-cyclohexadienylgroup, a 2,4-cycloheptadienyl group, and a 1,5-cyclooctadienyl group. Atleast one hydrogen atom of the unsubstituted C₃-C₃₀ cycloalkenyl groupmay be substituted with the same substituent as in the substitutedC₁-C₆₀ alkyl group described above.

As used herein, the unsubstituted C₆-C₆₀ aryl group indicates amonovalent group having an aromatic carbocyclic system that has 6 to 60carbon atoms and at least one aromatic ring and the unsubstituted C₆-C₆₀arylene group indicates a divalent group having an aromatic carbocyclicsystem that has 6 to 60 carbon atoms and at least one aromatic ring. Ifthe C₆-C₆₀ aryl group and the C₆-C₆₀ arylene group each independentlyhave two or more aromatic rings, the rings may be fused with each other.At least one hydrogen atom of each of the unsubstituted C₆-C₆₀ arylgroup and the unsubstituted C₆-C₆₀ arylene group may be substituted withthe same substituent as in the substituted C₁-C₆₀ alkyl group describedabove.

As used herein, examples of the substituted or unsubstituted C₆-C₆₀ arylgroup include, but not limited to, a phenyl group, a C₁-C₁₀ alkylphenylgroup (e.g., an ethylphenyl group), a C₁-C₁₀ alkylbiphenyl group (e.g.,an ethylbiphenyl group), a halophenyl group (e.g., an o-, m- andp-fluorophenyl group, and a dichlorophenyl group), a dicyanophenylgroup, a trifluoromethoxyphenyl group, an o-, m-, and p-tolyl group, ano-, m- and p-cumenyl group, a mesityl group, a phenoxyphenyl group, an(α,α-dimethylbenzene)phenyl group, a (N,N′-dimethyl)aminophenyl group, a(N,N′-diphenyl)aminophenyl group, a pentalenyl group, an indenyl group,a naphthyl group, a halonaphthyl group (e.g., a fluoronaphthyl group), aC₁-C₁₀ alkylnaphthyl group (e.g., a methylnaphthyl group), a C₁-C₁₀alkoxynaphthyl group (e.g., a methoxynaphthyl group), an anthracenylgroup, an azulenyl group, a heptalenyl group, an acenaphthylenyl group,a phenalenyl group, a fluorenyl group, an anthraquinolinyl group, amethylanthracenyl group, a phenanthrenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, an ethyl-chrysenyl group, a picenylgroup, a perylenyl group, a chloroperylenyl group, a pentaphenyl group,a pentacenyl group, a tetraphenylenyl group, a hexaphenyl group, ahexacenyl group, a rubicenyl group, a coroneryl group, a trinaphthylenylgroup, a heptaphenyl group, a heptacenyl, a pyranthrenyl group, and anovalenyl group. Examples of the substituted C₆-C₆₀ aryl group may beeasily understood with reference to the examples of the unsubstitutedC₆-C₆₀ aryl group described above and the substituents of thesubstituted C₁-C₆₀ alkyl group. Examples of the substituted orunsubstituted C₆-C₆₀ arylene group may be easily understood withreference to the substituted or unsubstituted C₆-C₆₀ aryl groupdescribed above.

As used herein, the unsubstituted C₂-C₆₀ heteroaryl group indicates amonovalent group having at least one aromatic ring system includingcarbon rings and at least one hetero atom selected from the groupconsisting of N, O, P, and S as a ring-forming atom, and theunsubstituted C₂-C₆₀ heteroarylene group indicates a divalent grouphaving at least one aromatic ring system including carbon rings and atleast one hetero atom selected from the group consisting of N, O, P, andS. In this regard, if the C₂-C₆₀ heteroaryl group and the C₂-C₆₀heteroarylene group each independently have two or more aromatic rings,the rings may be fused with each other. At least one hydrogen atom ofeach of the unsubstituted C₂-C₆₀ heteroaryl group and the unsubstitutedC₂-C₆₀ heteroarylene group may be substituted with the same substituentsas in the C₁-C₆₀ alkyl group described above.

As used herein, examples of the unsubstituted C₂-C₆₀ heteroaryl groupinclude, but not limited to, a pyrazolyl group, an imidazolyl group, anoxazolyl group, a thiazolyl group, a triazolyl group, a tetrazolylgroup, an oxadiazolyl group, a pyridinyl group, a pyridazinyl group, apyrimidinyl group, a triazinyl group, a carbazolyl group, an indolylgroup, a quinolinyl group, an isoquinolinyl group, a benzoimidazolylgroup, an imidazopyridinyl group, and an imidazopyrimidinyl group.Examples of the unsubstituted C₂-C₆₀ heteroarylene group may be easilyunderstood with reference to the examples of the substituted orunsubstituted C₂-C₆₀ arylene group.

The substituted or unsubstituted C₆-C₆₀ aryloxy group has a formula of—OA₂, wherein A₂ is the substituted or unsubstituted C₆-C₆₀ aryl groupas described above, and the substituted or unsubstituted C₆-C₆₀ arylthiogroup has a formula of —SA₃, wherein A₃ is the substituted orunsubstituted C₆-C₆₀ aryl group described above.

The following Examples and Comparative Examples are provided in order tohighlight characteristics of one or more embodiments, but it will beunderstood that the Examples and Comparative Examples are not to beconstrued as limiting the scope of the embodiments, nor are theComparative Examples to be construed as being outside the scope of theembodiments. Further, it will be understood that the embodiments are notlimited to the particular details described in the Examples andComparative Examples.

EXAMPLES Synthesis Example 1 Synthesis of Compound 1

Synthesis of Intermediate 1

5 g (1 eq, 29.06 mmol) of 2-bromo-3-methylpyridine, 6.12 g (1.05 eq,30.52 mmol) 4-bromophenylboronic acid, and 1.34 g (0.04 eq, 1.16 mmol)of tetrakis(triphenylphosphine)palladium(0) (Pd(PPh₃)₄) were put into areaction flask and vacuum-dried, and the flask was filled with nitrogengas. 72 ml of toluene was added into the reaction flask to dissolve thecompounds. Then, 36 ml of ethanol and 36 ml (2.5 eq, 72.65 mmol) of 2.0M sodium carbonate aqueous solution were added thereto, and the mixturewas stirred while refluxing at a temperature of 120° C. for 3 hours.After the reaction was completed, the resultant solution was washed withdistilled water, and an organic layer was extracted and collected usingethyl acetate. The collected anhydrous organic layer was dried by usinganhydrous sulfur magnesium, and the solvent was removed therefrom bydistillation under reduced pressure. The residue obtained therefrom waspurified through a silica gel column chromatography to obtain 4.5 g(yield: 60%) of Intermediate 1. Intermediate 1 was confirmed by usingNMR and APCI-MS.

¹H-NMR δ(ppm): 8.50(d, 1H), 7.60(d, 3H), 7.42(td, 2H), 7.19(d, 1H),2.32(s, 3H)

APCI-MS (m/z): 248[M⁺]

Synthesis of Intermediate 2

5.88 g (1 eq, 21.14 mmol) of 2-(4-bromophenyl)nicotinic acid, which wasquantitatively obtained by reacting Intermediate 1 with a KMnO₄ aqueoussolution, was put into a reaction flask, and 30 g of polyphosphoric acidwas added thereto. After the reaction was completed, the resultingsolution was added into a beaker containing 5 N sodium hydroxide aqueoussolution, stirred at room temperature, and filtered the mixture toobtain 3.3 g (yield: 60%) of Intermediate 2 as a yellow solid.Intermediate 2 was confirmed by using NMR and APCI-MS.

¹H-NMR δ(ppm): 7.92(d, 1H), 7.86(s, 1H), 7.74(d, 2H), 7.25(d, 1H)

APCI-MS (m/z): 260[M⁺]

Synthesis of Intermediate 3

3.29 g (1 eq, 14.09 mmol) of 2-bromobiphenyl was put into a reactionflask and dissolved with 150 ml of THF. 4.67 ml (14.09 eq, 8.78 mmol) of1.6 M n-BuLi was slowly and added drop wise to the reaction flask at atemperature of −78° C. After stirring at a temperature of −78° C. for 30minutes, 3.3 g (0.9 eq, 12.69 mmol) of Intermediate 2 was added thereto,and then stirred at room temperature for 5 minutes. After the reactionwas completed, the resultant solution was washed with distilled water,and an organic layer was extracted and collected using ethyl acetate.The residue obtained from the collected organic layer by removing thesolvent was put into a flask, and 5 ml of MeSO₃H was slowly and addeddrop wise thereto. The reaction solution was extracted with ethylacetate, and an organic layer was collected. The collected anhydrousorganic layer was dried by using anhydrous sulfur magnesium, and thesolvent was removed therefrom by distillation under reduced pressure.The residue obtained therefrom was purified through a silica gel columnchromatography to obtain 3.4 g (yield: 70%) of Intermediate 3.Intermediate 2 was confirmed by using NMR and APCI-MS.

¹H-NMR δ(ppm): 8.59(t, 1H), 8.00(d, 1H), 7.85(d, 2H), 7.57(dd, 1H),7.41(t, 2H), 7.17(t, 2H), 7.06(d, 2H), 6.90(s, 1H), 6.74(d, 2H)

APCI-MS (m/z): 396[M⁺]

Synthesis of Compound 1

3.4 g (1 eq, 8.57 mmol) of Intermediate 3, 2.81 g (1.03 eq, 9.43 mmol)of 9-phenylanthracen-10-ylboronic acid, and 396 mg (0.04 eq, 0.343 mmol)Pd(PPh₃)₄ were put into a reaction flask and vacuum-dried, and the flaskwas filled with nitrogen gas. 40 ml of toluene was added into thereaction flask to dissolve the compounds. Then, 15 ml of ethanol and 15ml (2.5 eq, 21.4 mmol) of 2.0 M sodium carbonate aqueous solution wereadded thereto, and the mixture was stirred while refluxing at atemperature of 120° C. for 3 hours. After the reaction was completed,the resultant solution was washed with distilled water, and an organiclayer was extracted and collected using ethyl acetate. The collectedanhydrous organic layer was dried by using anhydrous sulfur magnesium,and the solvent was removed therefrom by distillation under reducedpressure. The residue obtained therefrom was purified through a silicagel column chromatography to obtain 3.8 g (yield: 78%) of Compound 1.Compound 1 was confirmed by using ¹H-NMR and APCI-MS.

¹H-NMR δ(ppm): 8.68(d, 1H), 8.39(d, 1H), 7.75(d, 2H), 7.58(m, 10H),7.47(d, 1H), 7.34(m, 4H), 7.24(d, 2H), 7.15(m, 4H), 6.87(m, 2H)

APCI-MS (m/z): 569[M⁺]

Synthesis Example 2 Synthesis of Compound 2

Synthesis of Intermediate 4

2.83 g (1 eq, 29.06 mmol) of methyl 2-chloronicotinate, 6.12 g (1.05 eq,30.52 mmol) of 4-bromophenylboronic acid, and 1.34 g (0.04 eq, 1.16mmol) of Pd(PPh₃)₄ were put into a reaction flask and vacuum-dried, andthe flask was filled with nitrogen gas. 72 ml of toluene was added intothe reaction flask to dissolve the compounds. Then, 36 ml of ethanol and36 ml (2.5 eq, 72.65 mmol) of 2.0 M sodium carbonate aqueous solutionwere added thereto, and the mixture was stirred while refluxing at atemperature of 120° C. for 3 hours. After the reaction was completed,the resultant solution was washed with distilled water, and an organiclayer was extracted and collected using ethyl acetate. The collectedanhydrous organic layer was dried by using anhydrous sulfur magnesium,and the solvent was removed therefrom by distillation under reducedpressure. The residue obtained therefrom was purified through a silicagel column chromatography to obtain 3.37 g (yield: 60%) of Intermediate4. Intermediate 4 was confirmed by using ¹H-NMR and APCI-MS.

¹H-NMR δ(ppm): 8.78(dd, 1H), 8.12(dd, 1H), 7.58(d, 2H), 7.42(d, 2H),7.34(d, 1H)

APCI-MS (m/z): 292[M⁺]

Synthesis of Intermediate 5

3.37 g (1 eq, 11.54 mmol) of Intermediate 4 was put into a reactionflask and vacuum-dried, and the flask was filled with nitrogen gas. 100ml of THF was added thereto, and then 9.6 ml (2.5 eq, 28.84 mmol) of 3.0M methylmagnesium chloride (CH₃MgCl) was slowly and added drop wisethereto. After the reaction was completed, the reaction solution wasextracted with ethyl acetate, and an organic layer was collected. Thecollected anhydrous organic layer was dried by using anhydrous sulfurmagnesium, and the solvent was removed therefrom by distillation underreduced pressure. The residue obtained therefrom was put into a flask,30 g of polyphosphoric acid was added thereto, and then the mixture wasstirred while refluxing at a temperature of 190° C. After the reactionwas completed, the reaction solution was extracted with ethyl acetate,and an organic layer was collected. The collected anhydrous organiclayer was dried by using anhydrous sulfur magnesium, and the solvent wasremoved therefrom by distillation under reduced pressure. The obtainedresidue was purified through a silica gel column chromatography toobtain 1.6 g (yield: 70%) of Intermediate 5. Intermediate 5 wasconfirmed by using ¹H-NMR and APCI-MS.

¹H-NMR δ(ppm): 8.56(d, 1H), 7.88(d, 1H), 7.72(d, 1H), 7.62(s, 1H),7.56(dd, 1H), 7.22(dd, 1H), 1.50(s, 6H)

APCI-MS (m/z): 274[M⁺]

Synthesis of Compound 2

1.6 g (1 eq, 5.83 mmol) of Intermediate 5, 1.91 g (1.1 eq, 6.42 mmol) of9-phenylanthracen-10-ylboronic acid, and 270 mg (0.04 eq, 0.23 mmol) ofPd(PPh₃)₄ were put into a reaction flask and vacuum-dried, and the flaskwas filled with nitrogen gas. 20 ml of toluene was added into thereaction flask to dissolve the compounds. Then, 9 ml of ethanol and 9 ml(3 eq, 17.5 mmol) of 2.0 M sodium carbonate aqueous solution were addedthereto, and the mixture was stirred while refluxing at a temperature of120° C. for 3 hours. After the reaction was completed, the resultantsolution was washed with distilled water, and an organic layer wasextracted and collected using ethyl acetate. The collected anhydrousorganic layer was dried by using anhydrous sulfur magnesium, and thesolvent was removed therefrom by distillation under reduced pressure.The residue obtained therefrom was purified through a silica gel columnchromatography to obtain 1.7 g (yield: 65%) of Compound 2. Compound 2was confirmed by using ¹H-NMR and APCI-MS.

¹H-NMR δ(ppm): 8.64(dd, 1H), 8.27(d, 1H), 7.73(m, 5H), 7.55(m, 7H),7.36(m, 4H), 7.27(t, 1H), 1.54(s, 6H)

APCI-MS (m/z): 447[M⁺]

Synthesis Example 3 Synthesis of Compound 3

Synthesis of Intermediate 6

Intermediate 6 was synthesized in the same manner as in the synthesis ofIntermediate 1, except that 2-bromophenyl boronic acid was used insteadof 4-bromobiphenyl. Intermediate 6 was confirmed by using ¹H-NMR andAPCI-MS.

¹H-NMR δ(ppm): 8.53(d, 1H), 7.67(d, 1H), 7.60(d, 1H), 7.40(t, 1H),7.29(m, 2H), 7. 22(m, 1H), 2.16(s, 3H)

APCI-MS (m/z): 248[M⁺]

Synthesis of Intermediate 7

3 g (yield: 89%) of Intermediate 7 was synthesized in the same manner asin the synthesis of Intermediate 2, except that Intermediate 6 was usedinstead of Intermediate 1. Intermediate 7 was confirmed by using ¹H-NMRand APCI-MS.

¹H-NMR δ(ppm): 8.80(dd, 1H), 7.94(d, 1H), 7.76(d, 1H), 7.72(d, 1H),7.29(m, 2H)

APCI-MS (m/z): 260[M⁺]

Synthesis of Intermediate 8

2.6 g (yield: 90%) of Intermediate 8 was synthesized in the same manneras in the synthesis of Intermediate 3, except that Intermediate 7 wasused instead of Intermediate 2. Intermediate 8 was confirmed by using¹H-NMR and APCI-MS.

¹H-NMR δ(ppm): 8.76(d, 1H), 7.85(d, 2H), 7.60(d, 1H), 7.40(t, 2H),7.15(t, 2H), 7.08(m, 3H), 6.70(t, 3H)

APCI-MS (m/z): 396[M⁺]

Synthesis of Compound 3

1.72 g (yield: 61%) of Compound 3 was synthesized in the same manner asin the synthesis of Compound 1, except that Intermediate 8 was usedinstead of Intermediate 3. Compound 3 was confirmed by using ¹H-NMR andAPCI-MS.

¹H-NMR δ(ppm): 7.90(d, 2H), 7.85(dd, 1H), 7.78(m, 4H), 7.64(m, 5H),7.42(t, 2H), 7.38(m, 6H), 7.22(d, 2H), 6.94(m, 4H), 6.68(dd, 1H)

APCI-MS (m/z): 569[M⁺]

Synthesis Example 4 Synthesis of Compound 4

Synthesis of Intermediate 9

3.25 g (yield: 47%) of Intermediate 9 was synthesized in the same manneras in the synthesis of Intermediate 4, except that 2-bromophenyl boronicacid was used instead of 4-bromobiphenyl boronic acid. Intermediate 9was confirmed by using ¹H-NMR and APCI-MS.

¹H-NMR δ(ppm): 8.83(d, 1H), 8.35(d, 1H), 7.63(d, 1H), 7.45-7.38(m, 3H),7.29(d, 1H), 3.71(s, 3H)

APCI-MS (m/z): 292[M⁺]

Synthesis of Intermediate 10

1.13 g (yield: 60%) of Intermediate 10 was synthesized in the samemanner as in the synthesis of Intermediate 5, except that Intermediate 9was used instead of Intermediate 4, and CH₃MgBr was used instead ofCH₃MgCl. Intermediate 10 was confirmed by using ¹H-NMR and APCI-MS.

¹H-NMR δ(ppm): 8.73(dd, 1H), 7.74(dd, 1H), 7.60(dd, 1H), 7.45(dd, 1H),7.29-7.23(m, 2H), 1.48(s, 6H)

APCI-MS (m/z): 274[M⁺]

Synthesis of Compound 4

1.82 g (yield: 76%) of Compound 4 was synthesized in the same manner asin the synthesis of Compound 2, except that Intermediate 10 was usedinstead of Intermediate 5. Compound 4 was confirmed by using ¹H-NMR andAPCI-MS.

¹H-NMR δ(ppm): 7.82(dd, 1H), 7.74(d, 2H), 7.70-7.50(m, 10H),7.34-7.16(m, 5H), 6.88(dd, 1H), 1.64(s, 6H)

APCI-MS (m/z): 447[M⁺]

Example 1

As an anode, a 15 Ω/cm² (1200 Å) ITO glass substrate was cut to a sizeof 50 mm×50 mm×0.7 mm, washed with ultrasonic waves in isopropyl alcoholand pure water for 5 minutes each, and then cleaned with UV for 30minutes and ozone for 10 minutes. The ITO glass substrate was mounted ona vacuum depositor.

4,4′,4″-tris[2-naphthyl(phenyl)amino]triphenylamine (2-TNATA) wasdeposited on the ITO glass substrate to form a HIL having a thickness of600 Å and 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) was thendeposited on the HIL to form a HTL having a thickness of 300 Å.

Then, Compound 1 (as a host) and Compound 102 (as a dopant) wereco-deposited on the HTL at a weight ratio of 95:5 to form an EML havinga thickness of 200 Å.

Then, Compound 201 was vacuum-deposited on the EML to form an ETL havinga thickness of 300 Å, LiF was deposited on the ETL to form an EIL havinga thickness of 10 Å, and Al was deposited on the EIL to form a cathodehaving a thickness of 3,000 Å, thereby completing the manufacture of anOLED.

Example 2

An OLED was manufactured in the same manner as in Example 1, except thatCompound 2 was used instead of Compound 1 in the formation of the EML.

Example 3

An OLED was manufactured in the same manner as in Example 1, except thatCompound 3 was used instead of Compound 1 in the formation of the EML.

Example 4

An OLED was manufactured in the same manner as in Example 1, except thatCompound 4 was used instead of Compound 1 in the formation of the EML.

Comparative Example 1

An OLED was manufactured in the same manner as in Example 1, except that9,10-di(naphthalen-2-yl)anthracene (ADN) was used instead of Compound 1in the formation of the EML.

Comparative Example 2

An OLED was manufactured in the same manner as in Example 1, except thatCompound X was used instead of Compound 102 in the formation of the EML.

Comparative Example 3

An OLED was manufactured in the same manner as in Example 1, except thatCompound A was used instead of Compound 1 in the formation of the EML.

Comparative Example 4

An OLED was manufactured in the same manner as in Example 1, except thatCompound B was used instead of Compound 1 in the formation of the EML.

Evaluation Example

Driving voltage, brightness, and efficiency of the OLEDs of Examples 1through 4 and Comparative Examples 1 through 4 were evaluated using acurrent-voltmeter, Kethley SMU 236 (available from PhotoResearch), toapply a voltage to the OLEDs, and the results are shown in Table 1below.

TABLE 1 Driving Bright- Effi- Dopant voltage ness ciency Host materialmaterial (V) (cd/m²) (cd/A) Example 1 Compound 1 Compound 3.8 456 4.56102 Example 2 Compound 2 Compound 3.6 438 4.38 102 Example 3 Compound 3Compound 3.5 432 4.32 102 Example 4 Compound 4 Compound 3.7 428 4.28 102Comparative ADN Compound 4.4 328 3.28 Example 1 102 Comparative Compound1 Compound 4.3 346 3.46 Example 2 X Comparative Compound A Compound 4.5352 3.52 Example 3 102 Comparative Compound B Compound 4.2 363 3.63Example 4 102

Referring to Table 1, the OLEDs of Examples 1 through 4 exhibitexcellent driving voltage, high brightness, and higher efficiency, ascompared to the OLEDs of Comparative Examples 1 through 4.

By way of summation and review, an OLED structure may include asubstrate, an anode, a hole transport layer (HTL), an emission layer(EML), an electron transport layer (ETL), and a cathode, which aresequentially stacked on the substrate. The HTL, the EML, and the ETL areorganic layers formed of organic compounds.

When a voltage is applied between the anode and the cathode, holesinjected from the anode move to the EML via the HTL, and electronsinjected from the cathode move to the EML via the ETL. The holes andelectrons are recombined with each other in the EML to generateexcitons. Then, the excitons are transitioned from an excited state to aground state, thereby generating light.

As described above, according to one or more embodiments, an OLED ofhigh quality may be provided.

Example embodiments have been disclosed herein, and although specificterms are employed, they are used and are to be interpreted in a genericand descriptive sense only and not for purpose of limitation. In someinstances, as would be apparent to one of ordinary skill in the art asof the filing of the present application, features, characteristics,and/or elements described in connection with a particular embodiment maybe used singly or in combination with features, characteristics, and/orelements described in connection with other embodiments unless otherwisespecifically indicated. Accordingly, it will be understood by those ofskill in the art that various changes in form and details may be madewithout departing from the spirit and scope of the present invention asset forth in the following claims. What is claimed is:

1.-20. (canceled)
 21. An indenopyridine-based compound represented byFormula 1:

wherein, in Formula 1, X₁ is a nitrogen atom (N) or C(R₁₁); X₂ is N orC(R₁₂); X₃ is N or C(R₁₃); X₄ is N or C(R₁₄); wherein only one of X₁ toX₄ is N; L₁ is selected from: i) an anthracenylene group, a chrysenylenegroup, and a pyrenylene group; and ii) an anthracenylene group, achrysenylene group, and a pyrenylene group, each substituted with atleast one selected from: a deuterium atom, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, a methyl group, an ethyl group, ann-propyl group, an iso-propyl group, an n-butyl group, a sec-butylgroup, an iso-butyl group, and a tert-butyl group; a phenyl group, anaphthyl group, a pyridyl group, and a triazinyl group; and a phenylgroup, a naphthyl group, a pyridyl group, and a triazinyl group, eachsubstituted with at least one selected from a deuterium atom, a halogenatom, a hydroxyl group, a cyano group, a nitro group, a methyl group, anethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, asec-butyl group, an iso-butyl group, and a tert-butyl group; n1 is 1, 2,or 3; R₁ and R₂ are each independently selected from a hydrogen atom, adeuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, a carboxyl group, a substituted or unsubstitutedC₁-C₃₀ alkyl group, a substituted or unsubstituted C₂-C₃₀ alkenyl group,a substituted or unsubstituted C₂-C₃₀ alkynyl group, a substituted orunsubstituted C₁-C₃₀ alkoxy group, a substituted or unsubstituted C₃-C₃₀cycloalkyl group and a substituted or unsubstituted C₃-C₃₀ cycloalkenylgroup, R₁₁ to R₁₄, R₃, and R₄ are each independently selected from ahydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, a carboxyl group, asubstituted or unsubstituted C₁-C₃₀ alkyl group, a substituted orunsubstituted C₂-C₃₀ alkenyl group, a substituted or unsubstitutedC₂-C₃₀ alkynyl group, a substituted or unsubstituted C₁-C₃₀ alkoxygroup, a substituted or unsubstituted C₃-C₃₀ cycloalkyl group, asubstituted or unsubstituted C₃-C₃₀ cycloalkenyl group, a substituted orunsubstituted C₆-C₃₀ aryl group, a substituted or unsubstituted C₆-C₃₀aryloxy group, and a substituted or unsubstituted C₆-C₃₀ arylthio group;and a1 and a2 are each independently selected from an integer of 0, 1, 2and
 3. 22. The indenopyridine-based compound as claimed in claim 21,wherein: L₁ is selected from an anthracenylene group, a chrysenylenegroup, and a pyrenylene group.
 23. The indenopyridine-based compound asclaimed in claim 21, wherein n1 is an integer of 1 or
 2. 24. Theindenopyridine-based compound as claimed in claim 21, wherein: a moietyrepresented by (L₁)_(n1) is one selected from Formulae 3-1 to 3-4:

wherein, in Formulae 3-1 to 3-4, * is a binding site with R₄, and ** isa binding site with an indenopyridine ring portion of Formula
 1. 25. Theindenopyridine-based compound as claimed in claim 21, wherein R₁ and R₂are each independently selected from a hydrogen atom, a deuterium atomand a methyl group.
 26. The indenopyridine-based compound as claimed inclaim 21, wherein R₁₁ to R₁₄, and R₃ are each independently selectedfrom a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group,a nitro group, and a methyl group.
 27. The indenopyridine-based compoundas claimed in claim 21, wherein: a2 is 1, 2, or 3, and R₄ is selectedfrom: i) a phenyl group, a naphthyl group, and an anthryl group; and ii)a phenyl group, a naphthyl group, and an anthryl group, each substitutedwith at least one selected from a hydrogen atom, a deuterium atom, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, a methylgroup, an ethyl group, an n-propyl group, an iso-propyl group, atert-butyl group, a phenyl group, a naphthyl group, and an anthrylgroup.
 28. The indenopyridine-based compound as claimed in claim 21,wherein: a2 is 1, 2, or 3, and R₄ is selected from a phenyl group, a1-naphthyl group, and a 2-naphthyl group.
 29. The indenopyridine-basedcompound as claimed in claim 21, wherein a2 is an integer of 0 or
 1. 30.The indenopyridine-based compound as claimed in claim 21, wherein: a2 is1; and a1 is
 3. 31. The indenopyridine-based compound as claimed inclaim 21, wherein the indenopyridine-based compound is represented byFormula 1a:

wherein, in Formula 1a, a moiety represented by (L₁)_(n1) is oneselected from Formulae 3-1 to 3-4:

wherein, in Formulae 3-1 to 3-4, * is a binding site with R₄, and ** isa binding site with an indenopyridine ring portion of Formula 1a; R₁ andR₂ are each independently selected from a hydrogen atom, a deuteriumatom and a methyl group, R₃ and R₁₂ to R₁₄ are each independentlyselected from a hydrogen atom, a deuterium atom, a fluorine atom, acyano group, a nitro group, and a methyl group; R₄ is selected from aphenyl group, a 1-naphthyl group, and a 2-naphthyl group; a1 is 3; anda2 is an integer of 0 or
 1. 32. The indenopyridine-based compound asclaimed in claim 21, wherein the indenopyridine-based compound isrepresented by one of Formulae 1b to 1e:

wherein, in Formulae 1b to 1e, a moiety represented by (L₁)_(n1) is oneselected from Formulae 3-1 to 3-4:

wherein, in Formulae 3-1 to 3-4, * is a binding site with R₄, and ** isa binding site with an indenopyridine ring portion of Formulae 1b to 1e;R₁ and R₂ are each independently selected from a hydrogen atom, adeuterium atom and a methyl group; R₁₃ is selected from a hydrogen atom,a deuterium atom, a fluorine atom, a cyano group, a nitro group, and amethyl group; R₄ is selected from a phenyl group, a 1-naphthyl group,and a 2-naphthyl group; and a2 is an integer of 0 or
 1. 33. Theindenopyridine-based compound as claimed in claim 21, wherein theindenopyridine-based compound represented by Formula 1 is one selectedfrom Compounds 2, 4, 6, 10, 14 and 17 to 19:


34. An organic light-emitting device (OLED), comprising: a firstelectrode; a second electrode facing the first electrode; and an organiclayer that is disposed between the first electrode and the secondelectrode and includes an emission layer, wherein the organic layerincludes at least one indenopyridine-based compound of claim
 21. 35. TheOLED as claimed in claim 34, wherein the organic layer further includesa hole transporting region including at least one selected from a holeinjection layer, a hole transport layer, a functional layer having bothhole injecting and transporting capabilities, a buffer layer, and anelectron blocking layer between the first electrode and the emissionlayer, and further includes an electron transporting region including atleast one selected from a hole blocking layer, an electron transportlayer, and an electron injection layer between the emission layer andthe second electrode.
 36. The OLED as claimed in claim 34, wherein theemission layer includes the indenopyridine-based compound.
 37. The OLEDas claimed in claim 36, wherein the emission layer further includes adopant, and the indenopyridine-based compound serves as a host.
 38. TheOLED as claimed in claim 37, wherein the dopant is an amine-basedcompound represented by Formula 100:

wherein, in Formula 100, X is selected from an anthracenyl group, achrysenyl group, a pyrenyl group, and a benzopyrenyl group; Ar₁₀₁ andAr₁₀₂ are each independently selected from i) a phenyl group, a naphthylgroup, and a biphenyl group; and ii) a phenyl group, a naphthyl group,and a biphenyl group, each substituted with at least one of a deuteriumatom, a fluorine atom, a cyano group, a nitro group, a methyl group, anethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, asec-butyl group, an iso-butyl group, a tert-butyl group, and a phenylgroup; and n is an integer of 2 to
 4. 39. The OLED as claimed in claim37, wherein the dopant is one selected from Compounds 101 to 109: